The Soccer Saturday presenter is part of an intrepid group of 18 that will tackle Africa's highest mountain in June to raise money for the Finlay Cooper Fund.
You can show your support now by making a donation at http://uk.virginmoneygiving.com/giving/ and searching for Jeff's name.
So how are preparations going? Let's see what's happening...
So, Jeff, have you ever attempted anything like this before?
JEFF: No. It's a crazy idea. I'm 58 years of age and while I've run eight marathons in different parts of the country they were all a long time ago and, for the most part, not uphill! A local newspaper reporter asked me this week 'is it true that you're climbing Everest'? No, we're climbing Kilimanjaro but this is my personal Everest. I'm looking forward to it with a bit of trepidation. I've been saying for a while that my football team, Hartlepool, has got a mountain to climb if they are to avoid relegation from League One but now I've got a bigger one!
How is the training going?
JEFF: This is the sort of thing you can't really train for - you just need to be reasonably fit and maybe do a couple of hill-walks in preparation. I've been training hard on the golf course and let me tell you, some of those bunkers are quite hard to climb out of! Fitness isn't really the biggest issue - the eldest man to have made the climb is around 80; the largest concern is coping with altitude. There's nothing remotely resembling Mount Kilimanjaro in Hampshire so I'm not entirely sure how I'm going to prepare for that.
In all seriousness, it's about taking as many precautions as you can. There are seven different routes up Kilimanjaro and we're taking the longest. The more time you take going up the mountain, the less likely you are to get altitude sickness. We'll take it slowly and hopefully it won't affect us too badly.
Do you know any good stats about Kilimanjaro?
JEFF: Alarmingly, I read that 10 people on average die every year attempting to trek up Kilimanjaro. When I signed up for this they told me it was easy!
We heard you're made of sterner stuff...
JEFF: I'm used to a comfortable, cushy lifestyle - I like my home comforts - but for a week I'll be trekking for how many hours are necessary, living in a tent and having one bowl of cold water a day to wash in. I hear the toilet facilities are going to be pretty primitive too. This simply doesn't happen at 'Stelling Mansions' so it's going to take a little getting used to but, of course, it's all in a great cause.
How supportive have the Soccer Saturday boys been?
JEFF: Let's just say I'm still waiting for their support to flood in, but I'm sure it will. I've had a lot of support since I first mentioned the idea from them and elsewhere, including a nice call from Jeremy Kyle who has had a few problems with his health and such like so it was good of him to take the time to say 'I'll definitely be supporting you'. To be fair Matt Le Tissier has already put his money where his mouth is.
How much are you hoping to raise?
JEFF: The target is simply to try and raise as much money as possible. There are 18 of us taking part so hopefully it will be a case of the bigger, the better!
So tell us about the fund...
JEFF: The Finlay Cooper Fund is not a big charity so the running costs are absolutely minimal. Finlay was the son of Colin Cooper, the former Middlesbrough and Nottingham Forest player. Tragically, Finlay choked to death just before his second birthday and his parents launched the Fund in his memory. It raises money principally for children's charities and hospices - that's where the money that we raise from the Kilimanjaro trek will go.
Colin is coming himself as is another former Middlesbrough footballer, Craig Hignett, and Graham Fordy who was Middlesbrough director. Thankfully, he's one person on the trek who is older than me! Everyone is going to have to get on well because we'll be living in pretty close proximity for the time that we're there. That should make egging each other on a lot easier.
Chris Kamara climbed Kilimanjaro a couple of years ago. Has he given you any advice?
JEFF: When I asked him about it he said it's one of the most worthwhile things he's ever done. He said he wouldn't do it again because it was tough - and I'll take heed of that because there are no guarantees that you'll make the top if altitude sickness gets in the way. In that scenario you have to turn back - it doesn't matter how fit you are. Chris got to the top but one or two others in his group, which included a lot of ex-professional sportsmen and such like, didn't make it.
What's the best piece of advice you've had so far?
JEFF: The Soccer Saturday boys all seem to be quite glad that I'm going! One or two of them say that I'm already over the hill, so I should just keep going and pretty soon I'll be over the mountain. No, look - if you've ever listened to them on Soccer Saturday you'll know that they tend not to talk much sense, so I won't be listening to their advice!
How can we keep track of your progress?
JEFF: I'm back on Twitter so I'll be tweeting about my progress @stellingjeff and, of course, I'll keep you posted on Soccer Saturday and in my skysports.com column. From this point it's a case of onwards and upwards, quite literally!
To find out more about Jeff's climb and make a donation visit http://uk.virginmoneygiving.com/giving/ and search for Jeff's name.